What Car Rental company will rent a car to a high risk driver?

You'll have to go with a local (non-chain) rental company. They tend to be more lax with the rules than the larger corporate establishments. They also tend to carry slightly older cars so they can take a bit more risk. Here in San Diego, Sensible Car Rental (http://sensible-car-rental.com) is an example of such an establishment. We are family owned and carry cars that are around 2-3 years old. As such, we can afford to rent to a riskier client base than a the larger establishements that carry brand new cars (and have top-down corporate rules to follow). You may want to search for "Discount Car Rental in [you city]". This will likely provide a list of local establishments that will be more flexible with their rules.